Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Chang Tong Yang' 'Daming Fan' 'Peng Foo Lee' 'John D. Ranford' 'Jagadese Vittal' _publ_contact_author_name 'Dr Chang Tong Yang' _publ_contact_author_address ; Department of Chemistry National University of Singapore 3 Science Singapore 117543 SINGAPORE ; _publ_contact_author_email CHMYCT@NUS.EDU.SG _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Chemical and Biological Studies of Dichloro(2-Phenylpyridine) Gold(III) Complex and Its Derivatives ; data_jdr32 _database_code_CSD 206807 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H8 Au Cl2 N' _chemical_formula_weight 422.05 _chemical_melting_point ? _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.9383(8) _cell_length_b 10.0796(6) _cell_length_c 7.8432(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.940(2) _cell_angle_gamma 90.00 _cell_volume 1097.82(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2105 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 29.2 _exptl_crystal_description 'platy, cut' _exptl_crystal_colour 'creamy yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.554 _exptl_crystal_density_method ? _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 13.848 _exptl_absorpt_correction_type 'sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.1637 _exptl_absorpt_correction_T_max 0.4050 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD System' _diffrn_measurement_method 'frames \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3495 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0780 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 29.20 _reflns_number_total 2274 _reflns_number_observed 1885 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ; riding models ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.31(3) _refine_ls_number_reflns 2274 _refine_ls_number_parameters 137 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_obs 0.0487 _refine_ls_wR_factor_all 0.1099 _refine_ls_wR_factor_obs 0.1045 _refine_ls_goodness_of_fit_all 1.030 _refine_ls_goodness_of_fit_obs 1.082 _refine_ls_restrained_S_all 1.030 _refine_ls_restrained_S_obs 1.081 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 3.382 _refine_diff_density_min -1.666 _refine_diff_density_rms 0.245 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Au1 Au 0.67411(8) 0.02038(4) 0.08661(11) 0.0390(2) Uani 1 d . . C1 C 0.5524(13) 0.0604(18) 0.1812(22) 0.045(4) Uani 1 d . . C2 C 0.5061(13) 0.1786(18) 0.2140(24) 0.058(5) Uani 1 d . . H2 H 0.5362(13) 0.2578(18) 0.1894(24) 0.069 Uiso 1 calc R . C3 C 0.4198(13) 0.1846(21) 0.2797(26) 0.069(6) Uani 1 d . . H3 H 0.3924(13) 0.2668(21) 0.2992(26) 0.083 Uiso 1 calc R . C4 C 0.3724(16) 0.0720(28) 0.3175(26) 0.073(6) Uani 1 d . . H4 H 0.3142(16) 0.0790(28) 0.3664(26) 0.087 Uiso 1 calc R . C5 C 0.4076(16) -0.0513(24) 0.2862(25) 0.065(5) Uani 1 d . . H5 H 0.3757(16) -0.1287(24) 0.3126(25) 0.078 Uiso 1 calc R . C6 C 0.4967(16) -0.0523(25) 0.2103(37) 0.039(6) Uani 1 d . . C7 C 0.5436(11) -0.1843(16) 0.1737(19) 0.041(4) Uani 1 d . . C8 C 0.5066(14) -0.3116(18) 0.1913(27) 0.066(5) Uani 1 d . . H8 H 0.4481(14) -0.3224(18) 0.2382(27) 0.080 Uiso 1 calc R . C9 C 0.5546(16) -0.4201(20) 0.1412(31) 0.080(6) Uani 1 d . . H9 H 0.5295(16) -0.5049(20) 0.1519(31) 0.096 Uiso 1 calc R . C10 C 0.6417(15) -0.4005(18) 0.0737(37) 0.082(7) Uani 1 d . . H10 H 0.6772(15) -0.4728(18) 0.0407(37) 0.098 Uiso 1 calc R . C11 C 0.6759(21) -0.2740(18) 0.0554(31) 0.052(7) Uani 1 d . . H11 H 0.7327(21) -0.2611(18) 0.0034(31) 0.063 Uiso 1 calc R . N1 N 0.6294(9) -0.1703(13) 0.1103(17) 0.043(3) Uani 1 d . . Cl1 Cl 0.8186(5) -0.0342(10) -0.0335(12) 0.073(3) Uani 1 d . . Cl2 Cl 0.7103(4) 0.2404(5) 0.0675(8) 0.071(2) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.0344(3) 0.0365(3) 0.0453(3) 0.0020(11) -0.0003(2) -0.0030(10) C1 0.046(10) 0.041(9) 0.050(10) 0.002(7) 0.009(8) -0.010(8) C2 0.053(11) 0.039(10) 0.078(12) -0.009(8) -0.010(9) 0.014(8) C3 0.055(13) 0.057(13) 0.093(15) -0.023(11) -0.010(10) 0.029(10) C4 0.059(13) 0.102(17) 0.055(12) -0.020(12) -0.008(9) 0.024(13) C5 0.063(13) 0.081(15) 0.051(11) -0.005(10) 0.002(9) 0.001(11) C6 0.028(13) 0.040(10) 0.046(11) -0.007(8) -0.019(10) 0.010(9) C7 0.033(8) 0.044(9) 0.043(9) 0.003(6) -0.015(6) 0.009(6) C8 0.054(12) 0.050(12) 0.095(14) 0.002(10) 0.004(10) -0.016(9) C9 0.078(16) 0.032(10) 0.127(18) 0.004(11) -0.018(13) -0.004(10) C10 0.063(16) 0.030(10) 0.147(21) -0.006(12) -0.017(17) 0.007(8) C11 0.034(8) 0.055(9) 0.068(21) -0.004(9) 0.006(11) -0.002(11) N1 0.033(7) 0.037(7) 0.058(8) -0.008(6) -0.005(6) -0.007(5) Cl1 0.042(4) 0.116(8) 0.060(4) -0.004(4) 0.008(4) -0.021(4) Cl2 0.074(4) 0.042(2) 0.097(4) 0.014(2) 0.005(3) -0.020(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 C1 1.95(2) . ? Au1 N1 2.034(13) . ? Au1 Cl2 2.282(5) . ? Au1 Cl1 2.361(8) . ? C1 C2 1.39(2) . ? C1 C6 1.41(3) . ? C2 C3 1.35(3) . ? C3 C4 1.36(3) . ? C4 C5 1.37(3) . ? C5 C6 1.42(3) . ? C6 C7 1.52(3) . ? C7 N1 1.34(2) . ? C7 C8 1.39(2) . ? C8 C9 1.36(3) . ? C9 C10 1.38(3) . ? C10 C11 1.37(3) . ? C11 N1 1.32(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Au1 N1 83.0(6) . . ? C1 Au1 Cl2 91.6(6) . . ? N1 Au1 Cl2 174.6(4) . . ? C1 Au1 Cl1 178.0(6) . . ? N1 Au1 Cl1 95.4(4) . . ? Cl2 Au1 Cl1 90.0(3) . . ? C2 C1 C6 113.0(18) . . ? C2 C1 Au1 132.9(14) . . ? C6 C1 Au1 113.9(15) . . ? C3 C2 C1 123.6(19) . . ? C2 C3 C4 120.7(18) . . ? C3 C4 C5 122.2(20) . . ? C4 C5 C6 114.9(23) . . ? C1 C6 C5 125.2(21) . . ? C1 C6 C7 115.1(19) . . ? C5 C6 C7 119.4(22) . . ? N1 C7 C8 118.9(15) . . ? N1 C7 C6 112.9(17) . . ? C8 C7 C6 128.2(18) . . ? C9 C8 C7 121.2(19) . . ? C8 C9 C10 117.8(19) . . ? C11 C10 C9 119.8(22) . . ? N1 C11 C10 121.1(26) . . ? C11 N1 C7 121.0(16) . . ? C11 N1 Au1 123.7(14) . . ? C7 N1 Au1 115.0(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Au1 C1 C2 -176.6(19) . . . . ? Cl2 Au1 C1 C2 2.8(19) . . . . ? Cl1 Au1 C1 C2 -138.2(172) . . . . ? N1 Au1 C1 C6 -2.2(15) . . . . ? Cl2 Au1 C1 C6 177.2(15) . . . . ? Cl1 Au1 C1 C6 36.1(187) . . . . ? C6 C1 C2 C3 4.9(29) . . . . ? Au1 C1 C2 C3 179.2(15) . . . . ? C1 C2 C3 C4 -0.2(31) . . . . ? C2 C3 C4 C5 -2.3(30) . . . . ? C3 C4 C5 C6 -0.4(26) . . . . ? C2 C1 C6 C5 -7.9(32) . . . . ? Au1 C1 C6 C5 176.6(19) . . . . ? C2 C1 C6 C7 179.2(17) . . . . ? Au1 C1 C6 C7 3.6(24) . . . . ? C4 C5 C6 C1 5.9(30) . . . . ? C4 C5 C6 C7 178.6(19) . . . . ? C1 C6 C7 N1 -3.4(25) . . . . ? C5 C6 C7 N1 -176.8(18) . . . . ? C1 C6 C7 C8 179.6(20) . . . . ? C5 C6 C7 C8 6.2(31) . . . . ? N1 C7 C8 C9 -1.8(29) . . . . ? C6 C7 C8 C9 175.0(20) . . . . ? C7 C8 C9 C10 0.6(33) . . . . ? C8 C9 C10 C11 -1.6(37) . . . . ? C9 C10 C11 N1 3.9(44) . . . . ? C10 C11 N1 C7 -5.2(38) . . . . ? C10 C11 N1 Au1 -179.4(19) . . . . ? C8 C7 N1 C11 4.1(27) . . . . ? C6 C7 N1 C11 -173.2(21) . . . . ? C8 C7 N1 Au1 178.8(13) . . . . ? C6 C7 N1 Au1 1.5(17) . . . . ? C1 Au1 N1 C11 174.9(20) . . . . ? Cl2 Au1 N1 C11 168.6(37) . . . . ? Cl1 Au1 N1 C11 -3.9(19) . . . . ? C1 Au1 N1 C7 0.3(11) . . . . ? Cl2 Au1 N1 C7 -5.9(53) . . . . ? Cl1 Au1 N1 C7 -178.4(10) . . . . ? data_jdr23 _database_code_CSD 206808 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H16 Au N O5' _chemical_formula_weight 487.25 _chemical_melting_point ? _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9815(1) _cell_length_b 9.5238(2) _cell_length_c 11.1538(2) _cell_angle_alpha 65.668(1) _cell_angle_beta 70.962(1) _cell_angle_gamma 64.721(1) _cell_volume 772.90(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4765 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 29.18 _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour 'purple black' _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.094 _exptl_crystal_density_method ? _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 9.539 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.3234 _exptl_absorpt_correction_T_max 0.8749 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD System' _diffrn_measurement_method 'frames \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4988 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 29.18 _reflns_number_total 3553 _reflns_number_observed 3215 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ; riding models ; _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0124(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3553 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_obs 0.0476 _refine_ls_wR_factor_all 0.1240 _refine_ls_wR_factor_obs 0.1205 _refine_ls_goodness_of_fit_all 1.025 _refine_ls_goodness_of_fit_obs 1.050 _refine_ls_restrained_S_all 1.025 _refine_ls_restrained_S_obs 1.050 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 2.113 _refine_diff_density_min -2.396 _refine_diff_density_rms 0.269 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Au1 Au 0.14627(3) 0.78383(3) 0.18555(2) 0.03113(15) Uani 1 d . . N1 N -0.0791(8) 0.7512(9) 0.2504(7) 0.0326(13) Uani 1 d . . O1 O 0.0529(9) 1.0402(7) 0.0971(6) 0.0425(14) Uani 1 d . . O2 O -0.0196(12) 1.0588(10) 0.3011(7) 0.072(2) Uani 1 d . . O3 O 0.3813(7) 0.7941(8) 0.1306(7) 0.0444(14) Uani 1 d . . O4 O 0.3836(8) 0.7587(10) -0.0555(7) 0.061(2) Uani 1 d . . C1 C 0.2262(11) 0.5402(10) 0.2727(8) 0.035(2) Uani 1 d . . C2 C 0.3908(11) 0.4406(11) 0.2794(9) 0.045(2) Uani 1 d . . H2 H 0.4767(11) 0.4843(11) 0.2402(9) 0.054 Uiso 1 calc R . C3 C 0.4260(12) 0.2707(12) 0.3468(10) 0.051(2) Uani 1 d . . H3 H 0.5365(12) 0.2024(12) 0.3514(10) 0.061 Uiso 1 calc R . C4 C 0.2993(13) 0.2040(10) 0.4063(10) 0.051(2) Uani 1 d . . H4 H 0.3242(13) 0.0921(10) 0.4504(10) 0.061 Uiso 1 calc R . C5 C 0.1350(11) 0.3064(11) 0.3991(9) 0.042(2) Uani 1 d . . H5 H 0.0496(11) 0.2620(11) 0.4382(9) 0.051 Uiso 1 calc R . C6 C 0.0951(9) 0.4753(10) 0.3341(8) 0.035(2) Uani 1 d . . C7 C -0.0735(10) 0.5947(9) 0.3180(7) 0.0328(15) Uani 1 d . . C8 C -0.2216(11) 0.5564(11) 0.3701(9) 0.040(2) Uani 1 d . . H8 H -0.2194(11) 0.4494(11) 0.4178(9) 0.048 Uiso 1 calc R . C9 C -0.3736(10) 0.6866(12) 0.3473(9) 0.046(2) Uani 1 d . . H9 H -0.4740(10) 0.6659(12) 0.3787(9) 0.056 Uiso 1 calc R . C10 C -0.3738(11) 0.8432(12) 0.2792(10) 0.049(2) Uani 1 d . . H10 H -0.4745(11) 0.9292(12) 0.2664(10) 0.058 Uiso 1 calc R . C11 C -0.2241(10) 0.8741(10) 0.2292(8) 0.038(2) Uani 1 d . . H11 H -0.2243(10) 0.9804(10) 0.1809(8) 0.046 Uiso 1 calc R . C12 C -0.0106(10) 1.1235(10) 0.1777(9) 0.041(2) Uani 1 d . . C13 C -0.0840(15) 1.3066(11) 0.1169(12) 0.055(2) Uani 1 d . . H13A H -0.0657(15) 1.3349(11) 0.0214(12) 0.083 Uiso 1 calc R . H13B H -0.0310(15) 1.3591(11) 0.1393(12) 0.083 Uiso 1 calc R . H13C H -0.2020(15) 1.3426(11) 0.1513(12) 0.083 Uiso 1 calc R . C14 C 0.4533(10) 0.7722(10) 0.0148(9) 0.043(2) Uani 1 d . . C15 C 0.6343(12) 0.7658(15) -0.0259(11) 0.061(3) Uani 1 d . . H15A H 0.6643(12) 0.7788(15) 0.0431(11) 0.091 Uiso 1 calc R . H15B H 0.6470(12) 0.8525(15) -0.1079(11) 0.091 Uiso 1 calc R . H15C H 0.7060(12) 0.6621(15) -0.0384(11) 0.091 Uiso 1 calc R . O5S O -0.7795(10) 0.8360(9) 0.4759(8) 0.061(2) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.0311(2) 0.0292(2) 0.0304(2) -0.01197(12) 0.00020(11) -0.00978(12) N1 0.024(3) 0.035(3) 0.033(3) -0.010(3) 0.000(2) -0.009(3) O1 0.059(4) 0.028(3) 0.033(3) -0.010(2) -0.001(3) -0.014(3) O2 0.106(6) 0.055(4) 0.047(4) -0.020(3) -0.024(4) -0.009(4) O3 0.030(3) 0.051(4) 0.056(4) -0.018(3) -0.003(3) -0.018(3) O4 0.046(4) 0.085(5) 0.047(4) -0.029(4) -0.002(3) -0.016(4) C1 0.040(4) 0.030(4) 0.031(4) -0.013(3) 0.001(3) -0.012(3) C2 0.035(4) 0.041(4) 0.048(5) -0.016(4) -0.003(3) -0.005(3) C3 0.045(5) 0.044(5) 0.055(5) -0.025(4) -0.013(4) 0.003(4) C4 0.071(6) 0.026(4) 0.057(5) -0.014(4) -0.025(5) -0.008(4) C5 0.041(4) 0.039(4) 0.046(4) -0.015(4) -0.001(3) -0.016(3) C6 0.029(3) 0.036(4) 0.035(4) -0.010(3) -0.004(3) -0.009(3) C7 0.039(4) 0.031(3) 0.028(3) -0.013(3) -0.001(3) -0.012(3) C8 0.039(4) 0.034(4) 0.048(4) -0.014(3) -0.006(3) -0.013(3) C9 0.030(4) 0.053(5) 0.051(5) -0.019(4) 0.000(3) -0.012(4) C10 0.037(4) 0.051(5) 0.060(5) -0.028(4) -0.010(4) -0.007(4) C11 0.037(4) 0.029(4) 0.039(4) -0.013(3) -0.011(3) 0.002(3) C12 0.036(4) 0.029(4) 0.059(5) -0.017(4) -0.015(4) -0.005(3) C13 0.061(6) 0.031(4) 0.069(6) -0.017(4) -0.016(5) -0.007(4) C14 0.035(4) 0.032(4) 0.047(5) -0.007(3) -0.010(3) -0.001(3) C15 0.037(5) 0.070(7) 0.063(6) -0.016(5) -0.005(4) -0.014(5) O5S 0.050(4) 0.051(4) 0.071(5) -0.019(4) -0.007(4) -0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 C1 2.005(8) . ? Au1 N1 2.028(6) . ? Au1 O3 2.031(6) . ? Au1 O1 2.108(6) . ? N1 C11 1.339(9) . ? N1 C7 1.352(10) . ? O1 C12 1.278(10) . ? O2 C12 1.245(11) . ? O3 C14 1.301(11) . ? O4 C14 1.222(11) . ? C1 C2 1.381(11) . ? C1 C6 1.408(11) . ? C2 C3 1.414(13) . ? C3 C4 1.384(15) . ? C4 C5 1.385(12) . ? C5 C6 1.399(11) . ? C6 C7 1.469(10) . ? C7 C8 1.405(12) . ? C8 C9 1.410(12) . ? C9 C10 1.366(13) . ? C10 C11 1.384(12) . ? C12 C13 1.507(12) . ? C14 C15 1.520(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Au1 N1 81.6(3) . . ? C1 Au1 O3 93.1(3) . . ? N1 Au1 O3 174.6(2) . . ? C1 Au1 O1 177.8(2) . . ? N1 Au1 O1 96.3(3) . . ? O3 Au1 O1 89.0(3) . . ? C11 N1 C7 121.6(7) . . ? C11 N1 Au1 123.3(6) . . ? C7 N1 Au1 115.1(5) . . ? C12 O1 Au1 115.7(5) . . ? C14 O3 Au1 111.2(6) . . ? C2 C1 C6 121.0(8) . . ? C2 C1 Au1 125.6(7) . . ? C6 C1 Au1 113.3(6) . . ? C1 C2 C3 118.6(9) . . ? C4 C3 C2 121.3(8) . . ? C3 C4 C5 119.1(8) . . ? C4 C5 C6 121.3(8) . . ? C5 C6 C1 118.7(7) . . ? C5 C6 C7 126.0(7) . . ? C1 C6 C7 115.3(7) . . ? N1 C7 C8 120.6(7) . . ? N1 C7 C6 114.7(7) . . ? C8 C7 C6 124.7(7) . . ? C7 C8 C9 117.3(8) . . ? C10 C9 C8 120.2(8) . . ? C9 C10 C11 120.1(8) . . ? N1 C11 C10 120.2(8) . . ? O2 C12 O1 122.7(8) . . ? O2 C12 C13 120.7(9) . . ? O1 C12 C13 116.5(8) . . ? O4 C14 O3 124.0(8) . . ? O4 C14 C15 122.8(8) . . ? O3 C14 C15 113.1(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Au1 N1 C11 -179.6(7) . . . . ? O3 Au1 N1 C11 172.4(22) . . . . ? O1 Au1 N1 C11 0.8(7) . . . . ? C1 Au1 N1 C7 0.7(6) . . . . ? O3 Au1 N1 C7 -7.4(26) . . . . ? O1 Au1 N1 C7 -179.0(5) . . . . ? C1 Au1 O1 C12 69.5(62) . . . . ? N1 Au1 O1 C12 78.5(6) . . . . ? O3 Au1 O1 C12 -100.7(6) . . . . ? C1 Au1 O3 C14 87.8(6) . . . . ? N1 Au1 O3 C14 95.8(24) . . . . ? O1 Au1 O3 C14 -92.6(6) . . . . ? N1 Au1 C1 C2 -179.6(8) . . . . ? O3 Au1 C1 C2 -0.4(8) . . . . ? O1 Au1 C1 C2 -170.5(57) . . . . ? N1 Au1 C1 C6 -1.9(6) . . . . ? O3 Au1 C1 C6 177.4(6) . . . . ? O1 Au1 C1 C6 7.2(64) . . . . ? C6 C1 C2 C3 1.3(13) . . . . ? Au1 C1 C2 C3 178.9(6) . . . . ? C1 C2 C3 C4 -0.4(13) . . . . ? C2 C3 C4 C5 0.0(14) . . . . ? C3 C4 C5 C6 -0.6(13) . . . . ? C4 C5 C6 C1 1.4(12) . . . . ? C4 C5 C6 C7 178.7(8) . . . . ? C2 C1 C6 C5 -1.8(12) . . . . ? Au1 C1 C6 C5 -179.7(6) . . . . ? C2 C1 C6 C7 -179.4(8) . . . . ? Au1 C1 C6 C7 2.8(9) . . . . ? C11 N1 C7 C8 -0.8(11) . . . . ? Au1 N1 C7 C8 178.9(6) . . . . ? C11 N1 C7 C6 -179.1(7) . . . . ? Au1 N1 C7 C6 0.6(8) . . . . ? C5 C6 C7 N1 -179.6(8) . . . . ? C1 C6 C7 N1 -2.3(10) . . . . ? C5 C6 C7 C8 2.2(13) . . . . ? C1 C6 C7 C8 179.6(7) . . . . ? N1 C7 C8 C9 0.8(12) . . . . ? C6 C7 C8 C9 178.9(8) . . . . ? C7 C8 C9 C10 -1.3(13) . . . . ? C8 C9 C10 C11 1.7(14) . . . . ? C7 N1 C11 C10 1.3(12) . . . . ? Au1 N1 C11 C10 -178.5(6) . . . . ? C9 C10 C11 N1 -1.7(13) . . . . ? Au1 O1 C12 O2 -1.0(12) . . . . ? Au1 O1 C12 C13 -177.7(7) . . . . ? Au1 O3 C14 O4 4.7(11) . . . . ? Au1 O3 C14 C15 -175.6(6) . . . . ? data_jdr22 _database_code_CSD 206809 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H23 Au N O4.50' _chemical_formula_weight 630.43 _chemical_melting_point ? _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.8963(2) _cell_length_b 16.8239(4) _cell_length_c 13.4511(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.522(1) _cell_angle_gamma 90.00 _cell_volume 2662.41(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5439 _cell_measurement_theta_min 1.95 _cell_measurement_theta_max 29.37 _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour beige _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method ? _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 5.557 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.3356 _exptl_absorpt_correction_T_max 0.1681 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD System' _diffrn_measurement_method 'frames \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15787 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.1022 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 29.37 _reflns_number_total 6429 _reflns_number_observed 3528 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ; riding models ; _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00007(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6429 _refine_ls_number_parameters 316 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1381 _refine_ls_R_factor_obs 0.0639 _refine_ls_wR_factor_all 0.1551 _refine_ls_wR_factor_obs 0.1351 _refine_ls_goodness_of_fit_all 1.043 _refine_ls_goodness_of_fit_obs 1.247 _refine_ls_restrained_S_all 1.045 _refine_ls_restrained_S_obs 1.249 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 1.530 _refine_diff_density_min -1.062 _refine_diff_density_rms 0.161 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Au1 Au 0.16274(3) 0.13371(2) 0.03104(3) 0.0534(2) Uani 1 d . . O1 O 0.3037(6) 0.1545(4) 0.1303(5) 0.065(2) Uani 1 d . . O2 O 0.3635(8) 0.2289(6) 0.0114(7) 0.110(3) Uani 1 d . . O3 O 0.0982(6) 0.2410(4) 0.0710(6) 0.068(2) Uani 1 d . . O4 O 0.0622(7) 0.1826(5) 0.2101(6) 0.085(2) Uani 1 d . . N1 N 0.0251(7) 0.1043(5) -0.0671(6) 0.053(2) Uani 1 d . . C1 C 0.2192(8) 0.0303(5) -0.0159(7) 0.048(2) Uani 1 d . . C2 C 0.3228(8) -0.0052(7) 0.0146(8) 0.063(3) Uani 1 d . . H2 H 0.3748(8) 0.0194(7) 0.0635(8) 0.076 Uiso 1 calc R . C3 C 0.3506(9) -0.0751(7) -0.0248(9) 0.075(3) Uani 1 d . . H3 H 0.4209(9) -0.0982(7) -0.0030(9) 0.090 Uiso 1 calc R . C4 C 0.2745(11) -0.1120(7) -0.0974(10) 0.078(4) Uani 1 d . . H4 H 0.2936(11) -0.1604(7) -0.1238(10) 0.094 Uiso 1 calc R . C5 C 0.1722(9) -0.0786(6) -0.1310(8) 0.063(3) Uani 1 d . . H5 H 0.1218(9) -0.1036(6) -0.1808(8) 0.076 Uiso 1 calc R . C6 C 0.1426(8) -0.0057(6) -0.0899(7) 0.052(2) Uani 1 d . . C7 C 0.0327(8) 0.0364(5) -0.1183(8) 0.055(3) Uani 1 d . . C8 C -0.0573(9) 0.0121(6) -0.1913(8) 0.065(3) Uani 1 d . . H8 H -0.0529(9) -0.0353(6) -0.2262(8) 0.078 Uiso 1 calc R . C9 C -0.1503(10) 0.0583(8) -0.2102(9) 0.081(4) Uani 1 d . . H9 H -0.2103(10) 0.0430(8) -0.2588(9) 0.097 Uiso 1 calc R . C10 C -0.1573(9) 0.1285(7) -0.1578(9) 0.073(3) Uani 1 d . . H10 H -0.2213(9) 0.1606(7) -0.1717(9) 0.088 Uiso 1 calc R . C11 C -0.0676(9) 0.1508(6) -0.0839(9) 0.062(3) Uani 1 d . . H11 H -0.0721(9) 0.1970(6) -0.0469(9) 0.075 Uiso 1 calc R . C12 C 0.3743(9) 0.2030(6) 0.0952(9) 0.060(3) Uani 1 d . . C13 C 0.4756(8) 0.2248(6) 0.1710(8) 0.055(3) Uani 1 d . . C14 C 0.5011(9) 0.1833(6) 0.2592(8) 0.066(3) Uani 1 d . . H14 H 0.4524(9) 0.1433(6) 0.2746(8) 0.079 Uiso 1 calc R . C15 C 0.5972(11) 0.2000(8) 0.3247(10) 0.086(4) Uani 1 d . . H15 H 0.6161(11) 0.1699(8) 0.3828(10) 0.103 Uiso 1 calc R . C16 C 0.6649(12) 0.2608(9) 0.3041(10) 0.090(4) Uani 1 d . . H16 H 0.7286(12) 0.2740(9) 0.3498(10) 0.108 Uiso 1 calc R . C17 C 0.6409(10) 0.3018(7) 0.2189(10) 0.081(4) Uani 1 d . . H17 H 0.6891(10) 0.3427(7) 0.2059(10) 0.097 Uiso 1 calc R . C18 C 0.5455(9) 0.2850(6) 0.1487(9) 0.070(3) Uani 1 d . . H18 H 0.5298(9) 0.3136(6) 0.0891(9) 0.084 Uiso 1 calc R . C19 C 0.0644(8) 0.2397(7) 0.1565(9) 0.061(3) Uani 1 d . . C20 C 0.0228(8) 0.3202(7) 0.1895(8) 0.059(3) Uani 1 d . . C21 C -0.0312(9) 0.3262(7) 0.2739(10) 0.075(3) Uani 1 d . . H21 H -0.0416(9) 0.2803(7) 0.3100(10) 0.090 Uiso 1 calc R . C22 C -0.0703(10) 0.3983(10) 0.3066(11) 0.092(4) Uani 1 d . . H22 H -0.1033(10) 0.4008(10) 0.3650(11) 0.110 Uiso 1 calc R . C23 C -0.0593(12) 0.4657(9) 0.2507(12) 0.096(4) Uani 1 d . . H23 H -0.0904(12) 0.5135(9) 0.2683(12) 0.115 Uiso 1 calc R . C24 C -0.0053(14) 0.4627(8) 0.1730(13) 0.116(5) Uani 1 d . . H24 H 0.0056(14) 0.5096(8) 0.1389(13) 0.140 Uiso 1 calc R . C25 C 0.0385(11) 0.3889(7) 0.1378(10) 0.082(4) Uani 1 d . . H25 H 0.0760(11) 0.3881(7) 0.0819(10) 0.098 Uiso 1 calc R . O5 O 0.6985(15) 0.4563(10) 0.0010(13) 0.123(7) Uani 0.50 d PD . C1S C 0.7505(20) 0.3354(12) -0.0698(19) 0.092(8) Uani 0.50 d PD . H1SA H 0.7714(20) 0.3127(12) -0.1300(19) 0.138 Uiso 0.50 calc PR . H1SB H 0.6830(20) 0.3100(12) -0.0544(19) 0.138 Uiso 0.50 calc PR . H1SC H 0.8112(20) 0.3277(12) -0.0151(19) 0.138 Uiso 0.50 calc PR . C2S C 0.7286(33) 0.4229(12) -0.0853(17) 0.151(14) Uiso 0.50 d PD . H2SA H 0.7965(33) 0.4487(12) -0.1017(17) 0.182 Uiso 0.50 calc PR . H2SB H 0.6679(33) 0.4309(12) -0.1411(17) 0.182 Uiso 0.50 calc PR . C3S C 0.6865(23) 0.5392(10) 0.0018(16) 0.103(9) Uiso 0.50 d PD . H3SA H 0.6351(23) 0.5564(10) -0.0570(16) 0.123 Uiso 0.50 calc PR . H3SB H 0.7596(23) 0.5644(10) 0.0007(16) 0.123 Uiso 0.50 calc PR . C4S C 0.6397(19) 0.5624(13) 0.0964(16) 0.081(7) Uani 0.50 d PD . H4SA H 0.6309(19) 0.6191(13) 0.0982(16) 0.122 Uiso 0.50 calc PR . H4SB H 0.6913(19) 0.5455(13) 0.1542(16) 0.122 Uiso 0.50 calc PR . H4SC H 0.5672(19) 0.5375(13) 0.0967(16) 0.122 Uiso 0.50 calc PR . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.0535(2) 0.0515(2) 0.0546(3) -0.0034(2) 0.0060(2) -0.0007(2) O1 0.059(4) 0.068(5) 0.063(5) 0.001(3) -0.010(4) -0.009(4) O2 0.098(7) 0.152(9) 0.069(6) 0.029(6) -0.021(5) -0.053(6) O3 0.086(5) 0.065(5) 0.055(5) -0.013(4) 0.013(4) 0.010(4) O4 0.117(7) 0.058(5) 0.085(6) -0.005(4) 0.028(5) -0.003(5) N1 0.056(5) 0.047(4) 0.055(5) -0.001(4) 0.010(4) 0.009(4) C1 0.051(5) 0.046(5) 0.047(6) 0.002(4) 0.010(4) -0.006(4) C2 0.051(6) 0.081(8) 0.056(7) 0.000(6) 0.003(5) 0.014(5) C3 0.064(7) 0.076(8) 0.089(9) -0.010(7) 0.025(7) 0.011(6) C4 0.088(9) 0.057(7) 0.096(10) -0.004(6) 0.032(8) 0.026(6) C5 0.069(7) 0.053(6) 0.069(7) -0.008(5) 0.017(6) 0.000(5) C6 0.054(6) 0.059(6) 0.046(6) 0.003(5) 0.018(5) 0.004(5) C7 0.057(6) 0.040(5) 0.069(7) 0.004(5) 0.013(5) -0.008(4) C8 0.059(7) 0.061(7) 0.074(8) -0.001(6) 0.004(6) -0.007(5) C9 0.069(8) 0.081(9) 0.084(9) 0.010(7) -0.014(7) -0.014(7) C10 0.052(6) 0.088(9) 0.078(8) 0.017(7) 0.004(6) 0.000(6) C11 0.054(6) 0.056(7) 0.078(8) 0.009(5) 0.012(5) -0.001(5) C12 0.061(7) 0.057(7) 0.060(7) -0.005(5) 0.000(5) -0.001(5) C13 0.048(5) 0.053(6) 0.061(7) -0.016(5) 0.000(5) 0.009(5) C14 0.078(8) 0.067(7) 0.050(6) -0.002(5) -0.004(6) 0.008(6) C15 0.080(9) 0.100(10) 0.073(9) 0.001(7) -0.005(7) 0.013(8) C16 0.083(9) 0.116(11) 0.061(8) -0.040(8) -0.020(7) 0.030(9) C17 0.066(7) 0.067(8) 0.102(10) -0.032(7) -0.007(7) -0.006(6) C18 0.064(7) 0.059(7) 0.081(8) -0.007(6) -0.006(6) -0.006(5) C19 0.048(6) 0.064(7) 0.066(8) -0.019(6) -0.008(5) 0.003(5) C20 0.044(5) 0.074(8) 0.059(7) -0.013(6) 0.005(5) -0.003(5) C21 0.057(7) 0.073(8) 0.092(9) -0.013(7) 0.006(6) -0.006(6) C22 0.064(8) 0.111(11) 0.102(11) -0.045(10) 0.020(7) -0.006(8) C23 0.106(11) 0.085(11) 0.099(12) -0.033(9) 0.027(9) 0.002(8) C24 0.163(16) 0.054(8) 0.128(14) -0.009(8) 0.006(12) 0.006(9) C25 0.091(9) 0.079(9) 0.076(8) -0.017(7) 0.017(7) -0.011(7) O5 0.087(12) 0.155(19) 0.121(17) -0.033(13) -0.004(11) 0.039(12) C1S 0.066(15) 0.136(23) 0.074(17) -0.012(15) 0.012(13) 0.022(15) C4S 0.085(17) 0.065(15) 0.093(19) -0.006(13) 0.009(14) -0.017(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 C1 2.001(9) . ? Au1 N1 2.007(8) . ? Au1 O1 2.014(6) . ? Au1 O3 2.063(7) . ? O1 C12 1.308(12) . ? O2 C12 1.197(12) . ? O3 C19 1.272(13) . ? O4 C19 1.204(13) . ? N1 C11 1.343(12) . ? N1 C7 1.344(12) . ? C1 C2 1.377(12) . ? C1 C6 1.385(12) . ? C2 C3 1.350(14) . ? C3 C4 1.38(2) . ? C4 C5 1.356(15) . ? C5 C6 1.411(13) . ? C6 C7 1.486(12) . ? C7 C8 1.403(13) . ? C8 C9 1.345(15) . ? C9 C10 1.38(2) . ? C10 C11 1.398(15) . ? C12 C13 1.505(13) . ? C13 C18 1.371(14) . ? C13 C14 1.372(14) . ? C14 C15 1.365(15) . ? C15 C16 1.36(2) . ? C16 C17 1.33(2) . ? C17 C18 1.393(14) . ? C19 C20 1.530(14) . ? C20 C25 1.38(2) . ? C20 C21 1.388(15) . ? C21 C22 1.39(2) . ? C22 C23 1.38(2) . ? C23 C24 1.31(2) . ? C24 C25 1.45(2) . ? O5 C2S 1.384(10) . ? O5 C3S 1.403(10) . ? C1S C2S 1.504(10) . ? C3S C4S 1.514(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Au1 N1 81.8(3) . . ? C1 Au1 O1 94.3(3) . . ? N1 Au1 O1 175.7(3) . . ? C1 Au1 O3 176.5(3) . . ? N1 Au1 O3 95.1(3) . . ? O1 Au1 O3 88.9(3) . . ? C12 O1 Au1 112.6(6) . . ? C19 O3 Au1 113.6(7) . . ? C11 N1 C7 121.6(9) . . ? C11 N1 Au1 122.5(7) . . ? C7 N1 Au1 115.9(6) . . ? C2 C1 C6 119.3(9) . . ? C2 C1 Au1 127.7(7) . . ? C6 C1 Au1 113.0(7) . . ? C3 C2 C1 121.4(10) . . ? C2 C3 C4 119.8(11) . . ? C5 C4 C3 120.9(10) . . ? C4 C5 C6 119.5(10) . . ? C1 C6 C5 119.1(9) . . ? C1 C6 C7 115.9(8) . . ? C5 C6 C7 125.0(9) . . ? N1 C7 C8 120.3(9) . . ? N1 C7 C6 113.4(8) . . ? C8 C7 C6 126.3(9) . . ? C9 C8 C7 119.0(11) . . ? C8 C9 C10 120.5(11) . . ? C9 C10 C11 119.6(10) . . ? N1 C11 C10 119.0(10) . . ? O2 C12 O1 125.6(10) . . ? O2 C12 C13 120.9(10) . . ? O1 C12 C13 113.6(9) . . ? C18 C13 C14 120.1(9) . . ? C18 C13 C12 118.9(10) . . ? C14 C13 C12 120.9(10) . . ? C15 C14 C13 120.6(12) . . ? C16 C15 C14 119.3(12) . . ? C17 C16 C15 120.6(12) . . ? C16 C17 C18 121.9(13) . . ? C13 C18 C17 117.4(11) . . ? O4 C19 O3 126.3(10) . . ? O4 C19 C20 119.6(11) . . ? O3 C19 C20 114.0(10) . . ? C25 C20 C21 117.8(11) . . ? C25 C20 C19 121.5(11) . . ? C21 C20 C19 120.7(11) . . ? C20 C21 C22 122.5(13) . . ? C23 C22 C21 118.7(13) . . ? C24 C23 C22 120.2(14) . . ? C23 C24 C25 122.4(14) . . ? C20 C25 C24 118.1(13) . . ? C2S O5 C3S 116.7(11) . . ? O5 C2S C1S 110.0(15) . . ? O5 C3S C4S 108.3(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Au1 O1 C12 98.5(7) . . . . ? N1 Au1 O1 C12 122.2(38) . . . . ? O3 Au1 O1 C12 -80.0(7) . . . . ? C1 Au1 O3 C19 130.4(51) . . . . ? N1 Au1 O3 C19 103.9(7) . . . . ? O1 Au1 O3 C19 -74.5(7) . . . . ? C1 Au1 N1 C11 -179.7(8) . . . . ? O1 Au1 N1 C11 156.5(37) . . . . ? O3 Au1 N1 C11 -1.3(8) . . . . ? C1 Au1 N1 C7 -2.1(7) . . . . ? O1 Au1 N1 C7 -26.0(43) . . . . ? O3 Au1 N1 C7 176.3(7) . . . . ? N1 Au1 C1 C2 -179.9(9) . . . . ? O1 Au1 C1 C2 -1.7(9) . . . . ? O3 Au1 C1 C2 153.4(49) . . . . ? N1 Au1 C1 C6 2.2(7) . . . . ? O1 Au1 C1 C6 -179.6(7) . . . . ? O3 Au1 C1 C6 -24.5(56) . . . . ? C6 C1 C2 C3 -1.1(16) . . . . ? Au1 C1 C2 C3 -178.9(9) . . . . ? C1 C2 C3 C4 0.2(18) . . . . ? C2 C3 C4 C5 0.8(19) . . . . ? C3 C4 C5 C6 -1.0(18) . . . . ? C2 C1 C6 C5 1.0(14) . . . . ? Au1 C1 C6 C5 179.1(7) . . . . ? C2 C1 C6 C7 179.9(8) . . . . ? Au1 C1 C6 C7 -2.0(11) . . . . ? C4 C5 C6 C1 0.1(15) . . . . ? C4 C5 C6 C7 -178.8(10) . . . . ? C11 N1 C7 C8 -0.1(14) . . . . ? Au1 N1 C7 C8 -177.7(7) . . . . ? C11 N1 C7 C6 179.2(8) . . . . ? Au1 N1 C7 C6 1.6(10) . . . . ? C1 C6 C7 N1 0.3(12) . . . . ? C5 C6 C7 N1 179.2(9) . . . . ? C1 C6 C7 C8 179.6(9) . . . . ? C5 C6 C7 C8 -1.5(16) . . . . ? N1 C7 C8 C9 1.0(15) . . . . ? C6 C7 C8 C9 -178.2(10) . . . . ? C7 C8 C9 C10 -0.5(17) . . . . ? C8 C9 C10 C11 -0.9(18) . . . . ? C7 N1 C11 C10 -1.2(15) . . . . ? Au1 N1 C11 C10 176.2(7) . . . . ? C9 C10 C11 N1 1.8(16) . . . . ? Au1 O1 C12 O2 -5.2(15) . . . . ? Au1 O1 C12 C13 175.1(6) . . . . ? O2 C12 C13 C18 11.0(16) . . . . ? O1 C12 C13 C18 -169.3(9) . . . . ? O2 C12 C13 C14 -166.2(11) . . . . ? O1 C12 C13 C14 13.5(14) . . . . ? C18 C13 C14 C15 -1.5(16) . . . . ? C12 C13 C14 C15 175.6(10) . . . . ? C13 C14 C15 C16 3.2(18) . . . . ? C14 C15 C16 C17 -2.9(19) . . . . ? C15 C16 C17 C18 1.0(19) . . . . ? C14 C13 C18 C17 -0.4(15) . . . . ? C12 C13 C18 C17 -177.6(9) . . . . ? C16 C17 C18 C13 0.7(17) . . . . ? Au1 O3 C19 O4 -3.9(14) . . . . ? Au1 O3 C19 C20 176.7(6) . . . . ? O4 C19 C20 C25 170.8(10) . . . . ? O3 C19 C20 C25 -9.8(14) . . . . ? O4 C19 C20 C21 -8.5(15) . . . . ? O3 C19 C20 C21 171.0(9) . . . . ? C25 C20 C21 C22 0.7(16) . . . . ? C19 C20 C21 C22 180.0(9) . . . . ? C20 C21 C22 C23 2.7(17) . . . . ? C21 C22 C23 C24 -5.1(21) . . . . ? C22 C23 C24 C25 4.2(24) . . . . ? C21 C20 C25 C24 -1.8(16) . . . . ? C19 C20 C25 C24 179.0(10) . . . . ? C23 C24 C25 C20 -0.6(21) . . . . ? C3S O5 C2S C1S 173.7(22) . . . . ? C2S O5 C3S C4S 173.1(26) . . . . ? data_9928 _database_code_CSD 206810 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 Au N O4' _chemical_formula_weight 493.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.5342(2) _cell_length_b 21.1840(6) _cell_length_c 10.7191(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.3880(10) _cell_angle_gamma 90.00 _cell_volume 1454.53(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5061 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 29.39 _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.-4 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 10.135 _exptl_absorpt_correction_type 'sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.4054 _exptl_absorpt_correction_T_max 0.6429 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9349 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 29.39 _reflns_number_total 3486 _reflns_number_gt 2966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0178P)^2^+1.1767P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00029(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3486 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0546 _refine_ls_wR_factor_gt 0.0515 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.42731(2) 0.592425(8) 0.403038(14) 0.02834(7) Uani 1 1 d . . . O1 O 0.1995(4) 0.62514(16) 0.4838(3) 0.0392(7) Uani 1 1 d . . . O2 O 0.1044(5) 0.66141(18) 0.6557(3) 0.0510(9) Uani 1 1 d . . . O3 O 0.5864(4) 0.56005(15) 0.5780(3) 0.0339(7) Uani 1 1 d . . . O4 O 0.6471(6) 0.57137(17) 0.7861(3) 0.0455(8) Uani 1 1 d . . . N1 N 0.6318(5) 0.55748(16) 0.3044(3) 0.0277(7) Uani 1 1 d . . . C1 C 0.2887(6) 0.62150(19) 0.2295(4) 0.0283(9) Uani 1 1 d . . . C2 C 0.1125(7) 0.6578(2) 0.2029(4) 0.0385(11) Uani 1 1 d . . . H2A H 0.0465 0.6713 0.2675 0.046 Uiso 1 1 calc R . . C3 C 0.0341(8) 0.6743(2) 0.0761(5) 0.0474(13) Uani 1 1 d . . . H3 H -0.0846 0.6994 0.0563 0.057 Uiso 1 1 calc R . . C4 C 0.1303(8) 0.6537(2) -0.0203(4) 0.0452(12) Uani 1 1 d . . . H4 H 0.0745 0.6639 -0.1045 0.054 Uiso 1 1 calc R . . C5 C 0.3098(7) 0.6178(2) 0.0091(4) 0.0378(10) Uani 1 1 d . . . H5 H 0.3764 0.6044 -0.0553 0.045 Uiso 1 1 calc R . . C6 C 0.3910(7) 0.60185(18) 0.1342(4) 0.0291(9) Uani 1 1 d . . . C7 C 0.5838(6) 0.5657(2) 0.1758(4) 0.0274(8) Uani 1 1 d . . . C8 C 0.7144(7) 0.5418(2) 0.1012(4) 0.0342(10) Uani 1 1 d . . . H8 H 0.6854 0.5482 0.0136 0.041 Uiso 1 1 calc R . . C9 C 0.8880(7) 0.5082(2) 0.1576(4) 0.0381(10) Uani 1 1 d . . . H9 H 0.9769 0.4918 0.1078 0.046 Uiso 1 1 calc R . . C10 C 0.9315(7) 0.4987(2) 0.2863(4) 0.0398(11) Uani 1 1 d . . . H10 H 1.0476 0.4752 0.3241 0.048 Uiso 1 1 calc R . . C11 C 0.8010(7) 0.5243(2) 0.3588(4) 0.0365(10) Uani 1 1 d . . . H11 H 0.8302 0.5185 0.4466 0.044 Uiso 1 1 calc R . . C12 C 0.2416(7) 0.6479(2) 0.6010(4) 0.0342(10) Uani 1 1 d . . . C13 C 0.4733(6) 0.6569(2) 0.6611(4) 0.0301(9) Uani 1 1 d . . . C14 C 0.5164(7) 0.7005(2) 0.7785(4) 0.0391(11) Uani 1 1 d . . . H14A H 0.3942 0.7235 0.7922 0.047 Uiso 1 1 calc R . . H14B H 0.5849 0.6794 0.8558 0.047 Uiso 1 1 calc R . . C15 C 0.6632(8) 0.7399(2) 0.7168(5) 0.0514(13) Uani 1 1 d . . . H15A H 0.8095 0.7333 0.7540 0.062 Uiso 1 1 calc R . . H15B H 0.6294 0.7845 0.7124 0.062 Uiso 1 1 calc R . . C16 C 0.5913(7) 0.7050(2) 0.5909(4) 0.0410(11) Uani 1 1 d . . . H16A H 0.7045 0.6865 0.5569 0.049 Uiso 1 1 calc R . . H16B H 0.5002 0.7298 0.5268 0.049 Uiso 1 1 calc R . . C17 C 0.5782(6) 0.5923(2) 0.6811(4) 0.0307(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.02802(10) 0.03902(10) 0.01798(9) -0.00027(7) 0.00453(5) 0.00390(7) O1 0.0266(16) 0.063(2) 0.0279(16) -0.0077(15) 0.0050(12) 0.0075(14) O2 0.0353(19) 0.079(3) 0.042(2) -0.0123(19) 0.0155(15) 0.0085(17) O3 0.0426(18) 0.0408(17) 0.0185(14) 0.0033(13) 0.0065(12) 0.0128(14) O4 0.061(2) 0.0516(19) 0.0234(16) 0.0030(15) 0.0061(15) 0.0148(17) N1 0.0271(17) 0.0355(19) 0.0202(16) -0.0019(15) 0.0038(13) 0.0053(14) C1 0.033(2) 0.032(2) 0.0187(19) 0.0023(17) 0.0023(15) 0.0000(18) C2 0.038(3) 0.048(3) 0.030(2) 0.000(2) 0.0060(19) 0.005(2) C3 0.044(3) 0.054(3) 0.040(3) 0.005(2) -0.002(2) 0.018(2) C4 0.053(3) 0.054(3) 0.026(2) 0.004(2) 0.000(2) 0.014(2) C5 0.051(3) 0.044(2) 0.018(2) -0.0005(19) 0.0046(18) -0.001(2) C6 0.033(2) 0.029(2) 0.025(2) 0.0008(17) 0.0049(16) -0.0022(17) C7 0.031(2) 0.031(2) 0.0199(19) 0.0004(17) 0.0052(15) -0.0040(17) C8 0.040(2) 0.041(2) 0.022(2) -0.0045(19) 0.0082(17) -0.001(2) C9 0.035(2) 0.049(3) 0.034(2) -0.007(2) 0.0141(19) 0.005(2) C10 0.032(2) 0.053(3) 0.034(3) -0.001(2) 0.0061(19) 0.011(2) C11 0.034(2) 0.048(3) 0.026(2) 0.000(2) 0.0042(17) 0.006(2) C12 0.032(2) 0.039(2) 0.032(2) -0.0014(19) 0.0082(18) 0.0043(19) C13 0.030(2) 0.041(2) 0.021(2) -0.0025(18) 0.0092(16) 0.0027(18) C14 0.043(3) 0.042(3) 0.033(2) -0.008(2) 0.0088(19) -0.002(2) C15 0.052(3) 0.044(3) 0.059(3) -0.003(3) 0.012(3) -0.005(2) C16 0.038(3) 0.045(3) 0.041(3) 0.010(2) 0.009(2) 0.000(2) C17 0.026(2) 0.043(2) 0.024(2) 0.0021(19) 0.0065(15) 0.0037(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 O1 1.989(3) . ? Au1 C1 1.998(4) . ? Au1 N1 2.002(3) . ? Au1 O3 2.074(3) . ? O1 C12 1.323(5) . ? O2 C12 1.199(5) . ? O3 C17 1.309(5) . ? O4 C17 1.211(5) . ? N1 C11 1.343(5) . ? N1 C7 1.364(5) . ? C1 C2 1.367(6) . ? C1 C6 1.391(6) . ? C2 C3 1.399(6) . ? C3 C4 1.382(7) . ? C4 C5 1.380(6) . ? C5 C6 1.382(6) . ? C6 C7 1.467(6) . ? C7 C8 1.376(6) . ? C8 C9 1.374(6) . ? C9 C10 1.368(6) . ? C10 C11 1.374(6) . ? C12 C13 1.536(6) . ? C13 C17 1.528(6) . ? C13 C14 1.541(6) . ? C13 C16 1.558(6) . ? C14 C15 1.517(7) . ? C15 C16 1.528(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Au1 C1 93.28(15) . . ? O1 Au1 N1 173.57(12) . . ? C1 Au1 N1 81.36(15) . . ? O1 Au1 O3 90.35(12) . . ? C1 Au1 O3 176.37(14) . . ? N1 Au1 O3 95.02(12) . . ? C12 O1 Au1 120.5(3) . . ? C17 O3 Au1 119.6(3) . . ? C11 N1 C7 120.7(4) . . ? C11 N1 Au1 122.9(3) . . ? C7 N1 Au1 116.3(3) . . ? C2 C1 C6 121.5(4) . . ? C2 C1 Au1 125.2(3) . . ? C6 C1 Au1 113.4(3) . . ? C1 C2 C3 118.4(5) . . ? C4 C3 C2 120.9(4) . . ? C5 C4 C3 119.6(4) . . ? C4 C5 C6 120.1(5) . . ? C5 C6 C1 119.4(4) . . ? C5 C6 C7 124.4(4) . . ? C1 C6 C7 116.2(4) . . ? N1 C7 C8 119.7(4) . . ? N1 C7 C6 112.7(4) . . ? C8 C7 C6 127.6(4) . . ? C9 C8 C7 119.2(4) . . ? C10 C9 C8 120.6(4) . . ? C9 C10 C11 118.9(4) . . ? N1 C11 C10 120.7(4) . . ? O2 C12 O1 121.1(4) . . ? O2 C12 C13 122.4(4) . . ? O1 C12 C13 116.5(4) . . ? C17 C13 C12 109.0(4) . . ? C17 C13 C14 114.7(3) . . ? C12 C13 C14 115.0(4) . . ? C17 C13 C16 113.8(4) . . ? C12 C13 C16 114.8(3) . . ? C14 C13 C16 88.5(3) . . ? C15 C14 C13 90.2(4) . . ? C14 C15 C16 90.5(4) . . ? C15 C16 C13 89.1(3) . . ? O4 C17 O3 121.6(4) . . ? O4 C17 C13 122.2(4) . . ? O3 C17 C13 116.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Au1 O1 C12 -146.0(3) . . . . ? N1 Au1 O1 C12 -179(100) . . . . ? O3 Au1 O1 C12 34.0(3) . . . . ? O1 Au1 O3 C17 -35.1(3) . . . . ? C1 Au1 O3 C17 145(2) . . . . ? N1 Au1 O3 C17 148.5(3) . . . . ? O1 Au1 N1 C11 -145.1(11) . . . . ? C1 Au1 N1 C11 -178.9(4) . . . . ? O3 Au1 N1 C11 1.4(3) . . . . ? O1 Au1 N1 C7 30.9(14) . . . . ? C1 Au1 N1 C7 -2.9(3) . . . . ? O3 Au1 N1 C7 177.4(3) . . . . ? O1 Au1 C1 C2 7.0(4) . . . . ? N1 Au1 C1 C2 -176.6(4) . . . . ? O3 Au1 C1 C2 -173(2) . . . . ? O1 Au1 C1 C6 -173.8(3) . . . . ? N1 Au1 C1 C6 2.6(3) . . . . ? O3 Au1 C1 C6 6(2) . . . . ? C6 C1 C2 C3 1.0(7) . . . . ? Au1 C1 C2 C3 -179.9(4) . . . . ? C1 C2 C3 C4 0.9(8) . . . . ? C2 C3 C4 C5 -1.9(8) . . . . ? C3 C4 C5 C6 1.0(8) . . . . ? C4 C5 C6 C1 0.8(7) . . . . ? C4 C5 C6 C7 -178.1(4) . . . . ? C2 C1 C6 C5 -1.8(6) . . . . ? Au1 C1 C6 C5 179.0(3) . . . . ? C2 C1 C6 C7 177.1(4) . . . . ? Au1 C1 C6 C7 -2.1(5) . . . . ? C11 N1 C7 C8 -2.5(6) . . . . ? Au1 N1 C7 C8 -178.6(3) . . . . ? C11 N1 C7 C6 178.6(4) . . . . ? Au1 N1 C7 C6 2.5(4) . . . . ? C5 C6 C7 N1 178.6(4) . . . . ? C1 C6 C7 N1 -0.2(5) . . . . ? C5 C6 C7 C8 -0.2(7) . . . . ? C1 C6 C7 C8 -179.1(4) . . . . ? N1 C7 C8 C9 2.0(6) . . . . ? C6 C7 C8 C9 -179.2(4) . . . . ? C7 C8 C9 C10 -0.1(7) . . . . ? C8 C9 C10 C11 -1.3(7) . . . . ? C7 N1 C11 C10 1.1(7) . . . . ? Au1 N1 C11 C10 176.9(3) . . . . ? C9 C10 C11 N1 0.9(7) . . . . ? Au1 O1 C12 O2 -171.8(4) . . . . ? Au1 O1 C12 C13 9.0(5) . . . . ? O2 C12 C13 C17 114.3(5) . . . . ? O1 C12 C13 C17 -66.6(5) . . . . ? O2 C12 C13 C14 -16.2(6) . . . . ? O1 C12 C13 C14 163.0(4) . . . . ? O2 C12 C13 C16 -116.8(5) . . . . ? O1 C12 C13 C16 62.4(5) . . . . ? C17 C13 C14 C15 105.8(4) . . . . ? C12 C13 C14 C15 -126.6(4) . . . . ? C16 C13 C14 C15 -9.8(4) . . . . ? C13 C14 C15 C16 10.0(4) . . . . ? C14 C15 C16 C13 -9.9(4) . . . . ? C17 C13 C16 C15 -106.8(4) . . . . ? C12 C13 C16 C15 126.7(4) . . . . ? C14 C13 C16 C15 9.7(4) . . . . ? Au1 O3 C17 O4 170.9(3) . . . . ? Au1 O3 C17 C13 -8.0(5) . . . . ? C12 C13 C17 O4 -114.1(5) . . . . ? C14 C13 C17 O4 16.5(6) . . . . ? C16 C13 C17 O4 116.4(5) . . . . ? C12 C13 C17 O3 64.8(5) . . . . ? C14 C13 C17 O3 -164.6(4) . . . . ? C16 C13 C17 O3 -64.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 29.39 _diffrn_measured_fraction_theta_full 0.871 _refine_diff_density_max 0.946 _refine_diff_density_min -0.994 _refine_diff_density_rms 0.124